Sulfo-containing halophenylazodiamino, cyano pyridine compounds

ABSTRACT

Compounds useful for dyeing nylon, wool, and leather, having the formula: ##STR1## wherein X 1  is chlorine, bromine, methyl or trifluoromethyl, Y 3  is chlorine or bromine, and K 1  is a radical of the formula ##STR2## where R 3  is C 2  to C 4  hydroxyalkyl, methoxyethyl or methoxypropyl.

The present invention relates to compounds which, in the form of the free acids, are of the general formula I ##STR3## where X is fluorine, chlorine, bromine, methyl, trifluoromethyl, C₁ -C₄ -alkylsulfonyl, arylsulfonyl, acetyl or benzoyl, Y is hydrogen, fluorine, chlorine, bromine, sulfamyl, C₁ -C₄ -mono- or -dialkylsulfamyl, C₁ -C₄ -alkylsulfonyl, methyl or trifluoromethyl, Y¹ is hydrogen, hydroxysulfonyl, methyl or chlorine, Y² is hydrogen or hydroxysulfonyl and K is a radical of the formula ##STR4## either Y¹ or Y² being hydroxysulfonyl, and T is cyano or methylsulfonyl, R is hydrogen or C₁ -C₃ -alkyl, R¹ is hydrogen or alkyl or is benzyl, sulfobenzyl, phenylethyl, sulfophenylethyl, sulfophenylpropyl or C₁ -C₁₀ -alkyl which is unsubstituted or substituted by hydroxyl, cyano, C₁ -C₄ -alkanoyloxy or C₁ -C₈ -alkoxy, or is a radical of the formula ##STR5## R² is hydrogen or C₁ -C₈ -alkyl, R³ is hydrogen or allyl, or is C₁ -C₁₀ -alkyl which may or may not be interrupted by oxygen and is unsubstituted or substituted by hydroxyl, cyano, C₁ -C₄ -alkanoyloxy, C₁ -C₈ -alkoxy, cyclohexyloxy, phenyl, phenoxy, sulfophenoxy, sulfophenyl or hydroxysulfonyloxy, or is cyclopentyl, or is cyclohexyl which is unsubstituted or substituted by hydroxyl, hydroxyethoxy or methyl, or is pyrrolidonylalkyl, phenyl, methoxyphenyl, sulfophenyl, C₁ -C₄ -alkoxysulfophenyl or a radical of the formula ##STR6## or R² and R³, together with the nitrogen, form a saturated 5-membered or 6-membered ring, Z is phenyl which is unsubstituted or substituted by chlorine, methyl, methoxy or acetylamino, and A is a C₂ -C₁₀ -alkyl radical which may or may not be interrupted by oxygen.

Radicals R are, in addition to hydrogen, ethyl, propyl or, preferably, methyl. In addition to those already mentioned, specific examples of radicals R¹, R² and R³ (where these fall under the general definition) are:

1. Unsubstituted or substituted alkyl radicals: ##STR7##

2. unsubstituted or substituted cycloalkyl radicals ##STR8##

3. Aralkyl radicals: ##STR9## and those containing C₆ H₄ CH₃ instead of C₆ H₅.

4. Sulfophenyl radicals: ##STR10##

5. ##STR11## where n is 2, 3, 4 or 6, C₂ H₄ OCHO, C₂ H₄ OCOC₂ H₅, C₂ H₄ OCOCH₃, (C₂ H₄ O)₂ COCH₃, (C₂ H₄ O)₂ CHO, (CH₂)₃ OCOCH₃, C₃ H₆ OCOC₂ H₅ and (CH₂)₃ OCHO.

Examples of preferred substituents R¹ and R³ are: ##STR12##

Within the scope of the general definitions, specific examples of radicals X and Y, in addition to those stated above, are methyl, ethyl, butyl, phenyl, tolylsulfonyl and the radicals of the formulae SO₂ NHCH₃, SO₂ NHC₂ H₅, SO₂ NHC₃ H₇, SO₂ NHC₄ H₉, SO₂ N(CH₃)₂, SO₂ N(C₂ H₅)₂, SO₂ N(C₃ H₇)₂ or SO₂ N(C₄ H₉)₂.

The dyes according to the invention can be prepared by diazotizing a diazo component of an amine of the formula ##STR13## by a conventional method, and reacting the resulting diazonium salt with a coupling component of the formula H--K.

Of particular importance are compounds of formula Ia ##STR14## where X¹ is chlorine, bromine, methyl or trifluoromethyl, and K¹ is a radical of the formula ##STR15## where R³ has the stated meanings.

Other useful compounds are those of the formula Ib ##STR16## where K¹, X¹ and Y³ have the meanings given in the case of formula Ia.

Dyes of the formula Ia which possess only one sulfo group are particularly suitable for producing level dyeings on nylon. Because of their fast rate of dyeing, they are particularly suitable for trichromatic dyeing.

The good lightfastness on wool, the advantageous phototropic behavior and the very good levelness are also noteworthy.

Some compounds according to the invention are also useful for dyeing leather.

In the Examples which follow, parts and percentages are by weight, unless stated otherwise.

PREPARATION OF THE INTERMEDIATES (A) 2,4-Dichloroacetanilide

396 parts by volume of sulfuryl chloride are added to 270 parts of acetanilide in 1000 parts by volume of nitrobenzene in the course of 3 hours at from 50° to 70° C. (the chlorination is begun at a low temperature, which is then increased in order to suppress the precipitation of 2,4-dichloroacetanilide). When the addition of sulfuryl chloride is complete, stirring is continued for 1 hour from 70° to 75° C., after which dissolved hydrogen chloride is blown out with nitrogen. The mixture is then left to cool, whereupon 2,4-dichloroacetanilide is precipitated, and is isolated by being filtered off.

The product can be washed with water and dried to give 330 parts of 2,4-dichloroacetanilide, which contains about 5% of 2,4,6-trichloroacetanilide. If the nitrobenzene which is recovered as a filtrate, and in which some 2,4-dichloroacetanilide is still dissolved, is employed in a second experiment, the yield increases to 396 parts.

(B) 2,4-Dichloroaniline-6-sulfonic acid

204 parts of the crude 2,4-dichloroacetanilide are added to 300 parts of 100% strength sulfuric acid, while stirring. Thereafter, the mixture is heated further to 130° C., and 235 parts of chlorosulfonic acid are added dropwise at this temperature in such a manner that the hydrogen chloride gas liberated can readily be removed. Stirring is then continued at from 135° to 140° C. until the sulfonation is complete, this taking about 1 hour. The mixture is then left to cool to 50°-80° C., and is poured into 1300 parts by volume of water. After steam distillation for a short time, 10 parts of pure 2,4,6-trichloroaniline are obtained, as a by-product, in the distillate. The reaction mixture is then cooled to room temperature, and precipitated 2,4-dichloroaniline-6-sulfonic acid is filtered off and washed with dilute hydrochloric acid. 204 parts of 2,4-dichloroaniline-6-sulfonic acid (calculated as 100% pure) are obtained as a colorless aqueous paste, which can be used in moist form for diazotizations. H-NMR in D₂ O: 7.3 ppm, 7.6 ppm, J: 3 Hz (as the ammonium salt).

(C) 2,4-Dichloroaniline-5-sulfonic acid

204 parts of crude 2,4-dichloroacetanilide are carefully added to 600 parts of 23% strength oleum, and the mixture is heated to 140° C. and stirred at this temperature for 1 hour. It is then left to cool to 50°-80° C. and is poured into 1000 parts of water. 10 parts of 2,4,6-trichloroaniline are isolated by steam distillation, and the remaining mixture is filtered after it has cooled. The gray product isolated is stirred with about 5000 parts of water and neutralized with sodium hydroxide solution. A little active carbon is added, after which the mixture is heated to about 95° C. and filtered, and the resulting 2,4-dichloroaniline-5-sulfonic acid is precipitated from the filtrate by acidification and is isolated in a conventional manner after the mixture has cooled. The product still contains a small amount of 2,4-dichloroaniline-6-sulfonic acid, which can be removed by recrystallization from water. 2,4-Dichloroaniline-5-sulfonic acid is obtained as a colorless powder. Yield: about 140 parts. H-NMR in D₂ O: 7.45 ppm (as the ammonium salt).

EXAMPLE 1

19.5 parts of 2,4-dichloroaniline-6-sulfonic acid are dissolved in 200 parts by volume of hot water at pH 7.5-10, using sodium hydroxide solution. A wetting agent which is effective under acidic conditions and 27 parts by volume of a 23% strength aqueous sodium nitrite solution are added, and the mixture is cooled to 0°-5° C. 60 parts of ice are added, after which 55 parts of a 15-18% strength hydrochloric acid solution are introduced all at once, and the mixture is stirred for a further 3 hours at from 0° to 5° C. Thereafter, a solution or suspension of 21.2 parts of 2,6-bis-(3-hydroxypropylamino)-3-cyano-4-methylpyridine in 120 parts by volume of water and 7 parts by volume of concentrated hydrochloric acid is run in, stirring is continued for from 15 to 30 minutes, and the pH of the mixture is then slowly increased to 2-2.5 by adding sodium hydroxide solution or sodium formate. The acid formed as a result of the coupling reaction is then bound continuously by adding appropriate amounts of sodium hydroxide solution or sodium formate. When the reaction has been maintained at pH 2-2.5 for about 30-60 minutes, the pH of the mixture is increased to 3-3.5 by adding dilute sodium hydroxide solution or sodium acetate, and stirring is continued at this pH until the coupling is substantially complete. The pH of the mixture is then increased to 4.3-4.7 by adding dilute sodium hydroxide solution, after which the coupling reaction quickly ends. The resulting dye of the formula ##STR17## is precipitated virtually quantitatively by adding 80 parts of sodium chloride, and is then isolated by filtration. It is dried to give 42 parts of a reddish brown powder which still contains about 1 part of water-soluble salts in addition to 41 parts of the dye.

The dye dissolves in water to give a yellow solution and dyes nylon and wool in intense, lightfast, golden yellow hues. The absorption maximum of a solution of about 0.020 part of dye in 900 parts by volume of dimethylformamide and 150 parts by volume of glacial acetic acid is 427.5 nm.

The particular advantage of this dye is the high migrating power and the ability to dye nylon simultaneously with red and blue dyes. For example, a dye mixture of about 4 parts of this dye with about 4 parts of Acid Red 57 and 3 parts of Acid Blue 72 gives a (dark) brown. All three dyes dye nylon fabric at the same rate in the temperature range from 60° to 100° C., so that the dyeing always remains brown. The dye is also suitable for combination dyeing to achieve beige hues which are very light-fast and in particular are non-phototropic to light from incandescent lamps (no reversible change to a greener hue).

EXAMPLE 2

19.5 parts of 2,4-dichloroaniline-6-sulfonic acid are diazotized by a procedure similar to that described in Example 1. Excess nitrous acid is then destroyed in a conventional manner, and the diazonium salt mixture is buffered to pH 2-4 with sodium acetate. A solution of 16.7 parts of 1-(2-methoxyethyl)-6-hydroxy-3-cyano-4-methylpyrid-2-one in 200 parts by volume of water, 10 parts of 50% strength sodium hydroxide solution and 0.3 part of a dispersant which is effective under acidic conditions is then run in. The coupling mixture is stirred for a further 60-80 minutes, after which it is acidified to pH 0.3-0.5 with concentrated hydrochloric acid, and the precipitated dye of the formula ##STR18## is filtered off under suction, washed salt-free with a little water and dried to give 36 parts of a yellow powder. 20 parts of this powder are suspended in a mixture of 20 parts of butyldiglycol and 60 parts of 2- or 3-methoxypropanol, and the suspension is neutralized with lithium hydroxide. Clear filtration gives a honey yellow solution. This dye solution is very useful for dyeing leather lemon yellow by a conventional spray-dyeing method. The absorption maximum of the dye in a 9:1 dimethylformamide/glacial acetic acid mixture is determined as 412 nm.

EXAMPLE 3

22.1 parts of 2-trifluoromethyl-4-chloroaniline-6-sulfonic acid are diazotized by a procedure similar to that described in Example 1. 31 parts of the coupling component of the formula ##STR19## in the form of a roughly 50% strength water-moist paste, are then introduced into the diazonium salt mixture, after which the pH of the coupling mixture is brought to 4.5-5 with 25% strength sodium hydroxide solution. When coupling is complete, the mixture is neutralized with further sodium hydroxide solution and is then spray dried.

73 parts of a red powder are obtained. The resulting dye is of the formula ##STR20## and has an absorption maximum of 430 nm in a 9:1 dimethylformamide/glacial acetic acid mixture. It dyes wool and nylon in fast intense golden yellow hues.

EXAMPLE 4

19.5 parts of 2,4-dichloroaniline-6-sulfonic acid are diazotized by a procedure similar to that described in Example 1. When excess nitrous acid has been destroyed, 24.2 parts of 2-phenyl-4,6-bis-(3-hydroxypropylamino)-pyrimidine are added, and stirring is continued until the coupling component has dissolved. Thereafter, a dispersant which is highly effective at pH 7-10 is added and the pH of the coupling mixture is brought to 8.5-9.2 with sodium hydroxide solution and then with a little sodium carbonate solution (as a buffer). Stirring is continued overnight, and the resulting dye of the formula ##STR21## (λmax: 431.5 nm (CH₃)₂ NCHO/CH₃ CO₂ H=9:1) is then precipitated by adding about 30 parts of sodium chloride and acidifying the mixture to pH 4-4.5, and is isolated in a conventional manner to give about 50 parts of a reddish brown powder which dissolves in water to give a yellow solution and dyes nylon fabric and wool in very fast golden yellow hues. The dye has great migrating power.

                                      TABLE 1                                      __________________________________________________________________________      ##STR22##                                                                                                           λmax                              No.                                                                               R  R.sup.1   R.sup.2    R.sup.3                                                                           Hue     (nm)                                     __________________________________________________________________________      1 Cl H         C.sub.3 H.sub.6 OCH.sub.3                                                                 C.sub.3 H.sub.7                                                                   yellow  413                                       2 Cl H         C.sub.3 H.sub.6 OH                                                                        C.sub.3 H.sub.7                                                                   yellow  413                                       3 Cl H         C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                       CH.sub.3                                                                          yellow  411                                       4 Cl H         C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                       H  yellow  412                                       5 Cl H         C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                       CH.sub.3                                                                          yellow  409                                       6 Cl H         C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                                CH.sub.3                                                                          yellow  409                                       7 Cl H         C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                      CH.sub.3                                                                          yellow  409                                       8 Cl H         C.sub.3 H.sub.6 OCH.sub.3                                                                 CH.sub.3                                                                          yellow  410                                       9 Cl H         C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                          CH.sub.3                                                                          yellow  410                                      10 Cl C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                      H          CH.sub.3                                                                          yellow  412                                      11 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                        H          CH.sub.3                                                                          yellow  411                                      12 Cl C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OH                                                                        CH.sub.3                                                                          golden yellow                                                                          422                                      13 Cl CH.sub.3  C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                       CH.sub.3                                                                          golden yellow                                                                          420                                      14 Cl C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                       CH.sub.3                                                                          golden yellow                                                                          422                                      15 Cl C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                       CH.sub.3                                                                          golden yellow                                                                          421                                      16 Cl CH.sub.2 CHCH.sub.2                                                                      C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                       CH.sub.3                                                                          golden yellow                                                                          422                                      17 Cl CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                       CH.sub.3                                                                          golden yellow                                                                          420                                      18 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                              CH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub. 3                                                                         golden yellow                                                                          419                                      19 Cl (CH.sub.2).sub.3 OCH.sub.3                                                               CH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.3                                                                          golden yellow                                                                          421                                      20 Cl (CH.sub.2).sub.3 OCH.sub.3                                                               (CH.sub.2).sub.3 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          427                                      21 Cl                                                                                 ##STR23##                                                                               C.sub.2 H.sub.4 OCH.sub.3                                                                 CH.sub.3                                                                          golden yellow                                                                          422                                      22 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                              (CH.sub.2).sub.3 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          423                                      23 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                              CH.sub.2 CH.sub.2 OH                                                                      CH.sub.3                                                                          golden yellow                                                                          423                                      24 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                               ##STR24## CH.sub.3                                                                          golden yellow                                                                          423                                      25 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                              CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                        CH.sub.3                                                                          golden yellow                                                                          421                                      26 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                              (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                                                      CH.sub.3                                                                          golden yellow                                                                          423                                      27 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                              (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH                                                     CH.sub.3                                                                          golden yellow                                                                          423                                      28 Cl CH.sub.2 CH.sub.2 OCH.sub. 3                                                             (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          424                                      29 Cl                                                                                 ##STR25##                                                                               CH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.3                                                                          golden yellow                                                                          423                                      30 Cl                                                                                 ##STR26##                                                                               (CH.sub.2).sub.3 OCH.sub.3                                                                CH.sub.3                                                                          orange  423                                      31 Cl                                                                                 ##STR27##                                                                               (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          422                                      32 Cl                                                                                 ##STR28##                                                                               (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          orange  424                                      33 Cl                                                                                 ##STR29##                                                                               (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                         CH.sub.3                                                                          orange  424                                      34 Cl                                                                                 ##STR30##                                                                                ##STR31## CH.sub.3                                                                          orange  424                                      35 Cl (CH.sub.2).sub.3 OH                                                                      (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          425                                      36 Cl (CH.sub.2).sub.3 OH                                                                       ##STR32## CH.sub.3                                                                          golden yellow                                                                          426                                      37 Cl (CH.sub.2).sub.3 OH                                                                      (CH.sub.2).sub.2 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          426                                      38 Cl (CH.sub.2).sub.3 OH                                                                      (CH.sub.2).sub.3 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          427                                      39 Cl (CH.sub.2).sub.3 OH                                                                      (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                         CH.sub.3                                                                          golden yellow                                                                          426                                      40 Cl (CH.sub.2).sub.2 OH                                                                      (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          420                                      41 Cl (CH.sub.2).sub.2 OH                                                                      (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          423                                      42 Cl (CH.sub.2).sub.2 OH                                                                       ##STR33## CH.sub.3                                                                          golden yellow                                                                          423                                      43 Cl (CH.sub.2).sub.2 OH                                                                      (CH.sub.2).sub.2 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          421                                      44 Cl (CH.sub.2).sub.2 OH                                                                      (CH.sub.2).sub.3 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          423                                      45 Cl (CH.sub.2).sub.2 OH                                                                      (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                         CH.sub.3                                                                          golden yellow                                                                          423                                      46 Cl (CH.sub.2).sub.2 OH                                                                      C.sub.4 H.sub.9 (n)                                                                       CH.sub.3                                                                          golden yellow                                                                          427                                      47 Cl (CH.sub.2).sub.2 OH                                                                      (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                CH.sub.3                                                                          golden yellow                                                                          425                                      48 Cl (CH.sub.2).sub.2 OH                                                                      (CH.sub.2).sub.2 C.sub.6 H.sub.5                                                          CH.sub.3                                                                          golden yellow                                                                          422                                      49 Cl (CH.sub.2).sub.2 OH                                                                       ##STR34## CH.sub.3                                                                          golden yellow                                                                          422                                      50 Cl (CH.sub.2).sub.2 OH                                                                       ##STR35## CH.sub.3                                                                          golden yellow                                                                          423                                      51 Cl C.sub.2 H.sub.5                                                                           ##STR36## CH.sub.3                                                                          golden yellow                                                                          422                                      52 Cl C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                           CH.sub.3                                                                          golden yellow                                                                          420                                      53 Cl (CH.sub.2).sub.2 CN                                                                      (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          422                                      54 Cl (CH.sub.2).sub.5 CN                                                                      (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          423                                      55 Cl (CH.sub.2).sub.2 C.sub.6 H.sub.5                                                         (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          421                                      56 Cl                                                                                 ##STR37##                                                                               C.sub.4 H.sub.9 (n)                                                                       CH.sub.3                                                                          golden yellow                                                                          423                                      57 Cl CH.sub.2 CHCH.sub.2                                                                      (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          422                                      58 Cl CH.sub.2 CHCH.sub.2                                                                      (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          423                                      59 Br (CH.sub.2).sub.3 OH                                                                      (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          429                                      60 CF.sub.3                                                                          (CH.sub.2).sub.3 OH                                                                      (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          430                                      61 CF.sub.3                                                                          (CH.sub.2).sub.2 OCH.sub.3                                                               (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          428                                      62 Cl                                                                                 ##STR38##                                                                               (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          425                                      63 Cl                                                                                 ##STR39##                                                                               (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          426                                      64 Cl                                                                                 ##STR40##                                                                               (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          426                                      65 Cl                                                                                 ##STR41##                                                                               (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          424                                      66 Cl (CH.sub.2 ).sub.2 OCOCH.sub.3                                                            (CH.sub.2).sub.2 OCOCH.sub.3                                                              CH.sub.3                                                                          golden yellow                                                                          420                                      67 Cl (CH.sub.2).sub.3 OCHO                                                                    (CH.sub.2).sub.3 OCHO                                                                     CH.sub.3                                                                          golden yellow                                                                          421                                      68 Cl (CH.sub.2).sub.2 OCH.sub.3                                                               (CH.sub.2).sub.3 OCHO                                                                     CH.sub.3                                                                          golden yellow                                                                          421                                      69 Cl (CH.sub.2).sub.3 OCHO                                                                    (CH.sub.2).sub.2 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          421                                      70 Cl (CH.sub.2).sub.4 OH                                                                      (CH.sub.2).sub.4 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          430                                      71 Cl (CH.sub.2).sub.4 OH                                                                      (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          429                                      72 Cl (CH.sub.2).sub.4 OH                                                                      (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          429                                      73 Cl (CH.sub.2).sub.4 OH                                                                      (CH.sub.2).sub.2 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          428                                      __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR42##                                                                     No.                                                                               R.sup.1        R.sup.2  R.sup.3                                                                             Hue                                            __________________________________________________________________________         ##STR43##     C.sub.2 H.sub.5                                                                         H    golden yellow                                  2                                                                                  ##STR44##     C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                     orange                                         3                                                                                  ##STR45##     C.sub.4 H.sub.9 (n)                                                                     H    golden yellow                                  4                                                                                  ##STR46##     C.sub.3 H.sub.6 OCH.sub.3                                                               H    golden yellow                                  5                                                                                  ##STR47##     C.sub.2 H.sub.4 OCH.sub.3                                                               H    golden yellow                                  6                                                                                  ##STR48##     C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                        H    golden yellow                                  7                                                                                  ##STR49##     C.sub.3 H.sub.6 OH                                                                      H    golden yellow                                  8                                                                                  ##STR50##     C.sub.4 H.sub.8 OH                                                                      H    golden yellow                                  9                                                                                  ##STR51##     C.sub.4 H.sub.9 (n)                                                                     C.sub.4 H.sub.9 (n)                                                                 orange                                         10                                                                                 ##STR52##                                                                                     ##STR53##                                                                              H    golden yellow                                  11                                                                                 ##STR54##     C.sub.2 H.sub.4 OH                                                                      H    golden yellow                                  12                                                                                 ##STR55##     C.sub.3 H.sub.6 OH                                                                      H    golden yellow                                  13                                                                                 ##STR56##     C.sub.4 H.sub.9 (n)                                                                     H    golden yellow                                  14                                                                                 ##STR57##     C.sub.3 H.sub.6 OCH.sub.3                                                               H    golden yellow                                  15                                                                                 ##STR58##     C.sub.2 H.sub.4 OCH.sub.3                                                               H    golden yellow                                  16                                                                                 ##STR59##                                                                                     ##STR60##                                                                              H    golden yellow                                  17 C.sub.4 H.sub.8 OH                                                                             ##STR61##                                                                              H    golden yellow                                  18 C.sub.3 H.sub.6 OH                                                                             ##STR62##    orange                                         19 C.sub.2 H.sub.4 OCH.sub.3                                                                      ##STR63##    orange                                         20 C.sub.3 H.sub.6 OCH.sub.3                                                                      ##STR64##    orange                                         21 C.sub.3 H.sub.6 OH                                                                             ##STR65##    orange                                         __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________      ##STR66##                                                                                                                    λmax                     No.                                                                               R  R.sup.1      R.sup.2   R.sup.3   Hue     (nm)                            __________________________________________________________________________     1  Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OH                                                                       golden yellow                                                                          429                             2  Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                golden yellow                                                                          428                             3  Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OCH.sub.3                                                                golden yellow                                                                          430                             4  Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                         golden yellow                                                                          428                             5  Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                      yellow  427                             6  Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                               yellow  427                             7  Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH                                                      golden yellow                                                                          430                             8  Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                      golden yellow                                                                          430                             9  Cl C.sub.2 H.sub.4 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                yellow  426                             10 Cl C.sub.2 H.sub.4 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OCH.sub.3                                                                yellow  427                             11 Cl C.sub.2 H.sub.4 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OC.sub.3 H.sub.7                                                         yellow  428                             12 Cl C.sub.2 H.sub.4 OCH.sub.3                                                                   C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                yellow  426                             13 Cl C.sub.2 H.sub.4 OCH.sub.3                                                                   C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OCH.sub.3                                                                yellow  428                             14 Cl C.sub.3 H.sub.6 OCH.sub.3                                                                   C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OCH.sub.3                                                                golden yellow                                                                          429                             15 Cl                                                                                 ##STR67##   C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OCH.sub.3                                                                golden yellow                                                                          430                             16 Cl                                                                                 ##STR68##   C.sub.6 H.sub.5                                                                           ##STR69##                                                                               golden yellow                                                                          431                             17 Br                                                                                 ##STR70##   C.sub.6 H.sub.5                                                                           ##STR71##                                                                               golden yellow                                                                          431                             18 Br C.sub.3 H.sub.6 OH                                                                          C.sub.3 H.sub.6                                                                          C.sub.3 H.sub.6 OH                                                                       golden yellow                                                                          432                             19 Cl C.sub.3 H.sub.6 OH                                                                           ##STR72##                                                                               C.sub.3 H.sub.6 OH                                                                       golden yellow                                                                          432                             20 Cl C.sub.3 H.sub.6 OH                                                                           ##STR73##                                                                               C.sub.3 H.sub.6 OH                                                                       golden yellow                                                                          432                             21 Cl C.sub.4 H.sub.8 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.4 H.sub.8 OH                                                                       golden yellow                                                                          433                             22 Cl C.sub.2 H.sub.4 OH                                                                           ##STR74##                                                                               C.sub.2 H.sub.4 OH                                                                       golden yellow                                                                          431                             23 Cl                                                                                 ##STR75##                                                                                   ##STR76##                                                                               C.sub.2 H.sub.4 OH                                                                       yellow  428                             24 CF.sub.3                                                                          C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.6                                                                          C.sub.3 H.sub.6 OH                                                                       golden yellow                                                                          434                             25 CF.sub.3                                                                          C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OH                                                                       golden yellow                                                                          433                             26 CF.sub.3                                                                           ##STR77##   C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OH                                                                       golden yellow                                                                          433                             27 CF.sub.3                                                                           ##STR78##   C.sub.6 H.sub.5                                                                           ##STR79##                                                                               golden yellow                                                                          435                             28 CF.sub.3                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   C.sub.6 H.sub.5                                                                           ##STR80##                                                                               golden yellow                                                                          432                             29 CF.sub.3                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OH                                                                       golden yellow                                                                          432                             30 CF.sub.3                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OH                                                                       golden yellow                                                                          432                             31 CF.sub.3                                                                          C.sub. 3 H.sub.6 OCH.sub.3                                                                  C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OH                                                                       golden yellow                                                                          435                             32 CF.sub.3                                                                           ##STR81##                                                                                   ##STR82##                                                                               C.sub.2 H.sub.4 OH                                                                       golden yellow                                                                          433                             33 Cl                                                                                 ##STR83##   C.sub.6 H.sub.5                                                                           ##STR84##                                                                               golden yellow                                                                          434                             34 CH.sub.3                                                                          C.sub.2 H.sub.4 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OH                                                                       golden yellow                                                                          432                             __________________________________________________________________________

                  TABLE 4                                                          ______________________________________                                          ##STR85##                                                                                                              λmax                           No. R  R.sup.1  R.sup.2       R.sup.3                                                                             Hue   (nm)                                  ______________________________________                                          1Cl   Cl       C.sub.2 H.sub.4 OH                                                                           H    green-                                                                               412                                                                      ish                                                                            yellow                                       2Cl   Cl       C.sub.2 H.sub.4 OH                                                                           CH.sub.3                                                                            green-                                                                               412                                                                      ish                                                                            yellow                                       3Cl   Cl       C.sub.2 H.sub.4 OH                                                                           C.sub.2 H.sub.5                                                                     green-                                                                               411                                                                      ish                                                                            yellow                                       4Cl   Cl       C.sub.2 H.sub.4 OH                                                                           C.sub.3 H.sub.7                                                                     green-                                                                               410                                                                 (n)  ish                                                                            yellow                                       5Cl   Cl       C.sub.3 H.sub.6 OH                                                                           CH.sub.3                                                                            green-                                                                               412                                                                      ish                                                                            yellow                                       6Cl   Cl       C.sub.3 H.sub.6 OH                                                                           CH.sub.3                                                                            green-                                                                               412                                                                      ish                                                                            yellow                                       7Cl   Cl       C.sub.3 H.sub.6 OH                                                                           C.sub.3 H.sub.7                                                                     green-                                                                               411                                                                 (n)  ish                                                                            yellow                                       8Cl   Cl       C.sub.3 H.sub.6 OCOCH.sub.3                                                                  CH.sub.3                                                                            green-                                                                               413                                                                      ish                                                                            yellow                                       9Cl   Cl       C.sub.3 H.sub.6 OCH.sub.3                                                                    C.sub.3 H.sub.7                                                                     green-                                                                               412                                                                 (n)  ish                                                                            yellow                                      10Cl   Cl       C.sub.3 H.sub.6 OCH.sub.3                                                                    CH.sub.3                                                                            green-                                                                               412                                                                      ish                                                                            yellow                                      11Br   Cl       C.sub.3 H.sub.6 OCH.sub.3                                                                    CH.sub.3                                                                            green-                                                                               413                                                                      ish                                                                            yellow                                      12Cl   Cl       C.sub.3 H.sub.6 OCH.sub.3                                                                    H    green-                                                                               412                                                                      ish                                                                            yellow                                      13Cl   Cl       C.sub.6 H.sub.13 (n)                                                                         CH.sub.3                                                                            green-                                                                               413                                                                      ish                                                                            yellow                                      14Cl   Cl       C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                             CH.sub.3                                                                            green-                                                                               413                                                                      ish                                                                            yellow                                      15Cl   Cl       C.sub.3 H.sub.6 OC.sub.3 H.sub.7                                                             CH.sub.3                                                                            green-                                                                               412                                                                      ish                                                                            yellow                                      16Cl   Cl       C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                          CH.sub.3                                                                            green-                                                                               412                                                                      ish                                                                            yellow                                      17Cl   CF.sub.3 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                          CH.sub.3                                                                            green-                                                                               407                                                                      ish                                                                            yellow                                      18Cl   CF.sub.3 C.sub.6 H.sub.12 OH                                                                          CH.sub.3                                                                            green-                                                                               408                                                                      ish                                                                            yellow                                      19Cl   Cl       C.sub.6 H.sub.12 OH                                                                          CH.sub.3                                                                            green-                                                                               413                                                                      ish                                                                            yellow                                      20Cl   CF.sub.3 C.sub.3 H.sub.6 OCH.sub.3                                                                    CH.sub.3                                                                            green-                                                                               407                                                                      ish                                                                            yellow                                      21Cl   CF.sub.3 CH.sub.2 CH.sub.2C.sub.6 H.sub.5                                                             CH.sub.3                                                                            green-                                                                               407                                                                      ish                                                                            yellow                                      22Cl   CF.sub.3 CH.sub.2 CHCH.sub.2                                                                          CH.sub.3                                                                            green-                                                                               407                                                                      ish                                                                            yellow                                      23Cl   CF.sub.3 C.sub.6 H.sub.13 (n)                                                                         CH.sub.3                                                                            green-                                                                               408                                                                      ish                                                                            yellow                                      24Cl   CF.sub.3                                                                                 ##STR86##    CH.sub.3                                                                            green- ish yellow                                                                    407                                   25Cl   Cl                                                                                       ##STR87##    CH.sub.3                                                                            green- ish yellow                                                                    412                                   26Cl   Cl                                                                                       ##STR88##    CH.sub.3                                                                            green- ish yellow                                                                    413                                   27Cl   Cl       C.sub.4 H.sub.8 OH                                                                           CH.sub.3                                                                            green-                                                                               413                                                                      ish                                                                            yellow                                      28Cl   Cl       C.sub.6 H.sub.12 OH                                                                          CH.sub.3                                                                            green-                                                                               413                                                                      ish                                                                            yellow                                      29H    SO.sub.2 C.sub.6 H.sub.5                                                                C.sub.4 H.sub.8 OH                                                                           CH.sub.3                                                                            green-                                                                         ish                                                                            yellow                                      30H    SO.sub.2 C.sub.6 H.sub.5                                                                C.sub.3 H.sub.6 OH                                                                           CH.sub.3                                                                            green-                                                                         ish                                                                            yellow                                      31Cl   CH.sub.3 C.sub.3 H.sub.6 OH                                                                           CH.sub.3                                                                            green-                                                                               411                                                                      ish                                                                            yellow                                      32Cl   CH.sub.3 C.sub.2 H.sub.4 OH                                                                           CH.sub.3                                                                            green-                                                                               412                                                                      ish                                                                            yellow                                      33Cl   CH.sub.3 C.sub.3 H.sub.6 OCH.sub.3                                                                    CH.sub.3                                                                            green-                                                                               411                                                                      ish                                                                            yellow                                      34Cl   Br       C.sub.3 H.sub.6 OCH.sub.3                                                                    CH.sub.3                                                                            green-                                                                               413                                                                      ish                                                                            yellow                                      35Cl   Br       C.sub.3 H.sub.6 OH                                                                           CH.sub.3                                                                            green-                                                                               413                                                                      ish                                                                            yellow                                      36Cl   Br       C.sub.4 H.sub.8 OH                                                                           CH.sub.3                                                                            green-                                                                               413                                                                      ish                                                                            yellow                                      37CH.sub.3                                                                            Br       C.sub.4 H.sub.8 OH                                                                           CH.sub.3                                                                            green-                                                                               414                                                                      ish                                                                            yellow                                      38CH.sub.3                                                                            Br       C.sub.3 H.sub.6 OH                                                                           CH.sub.3                                                                            green-                                                                               414                                                                      ish                                                                            yellow                                      39CH.sub.3                                                                            Br       C.sub.3 H.sub.6 OCH.sub. 3                                                                   CH.sub.3                                                                            green-                                                                               414                                                                      ish                                                                            yellow                                      40CH.sub.3                                                                            Br       C.sub.2 H.sub.4 OCH.sub.3                                                                    CH.sub.3                                                                            green-                                                                               414                                                                      ish                                                                            yellow                                      ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                          ##STR89##                                                                                                            λmax                             No.  R      A                  Hue     (nm)                                    ______________________________________                                         1    Cl     C.sub.2 H.sub.4    greenish                                                                               413                                                                    yellow                                          2    Cl     C.sub.3 H.sub.6    greenish                                                                               413                                                                    yellow                                          3    Cl                                                                                     ##STR90##         greenish yellow                                                                        413                                     4    Cl     (CH.sub.2).sub.6   greenish                                                                               412                                                                    yellow                                          5    Cl     (CH.sub.2).sub.3 O(CH.sub.2).sub.3                                                                greenish                                                                               413                                                                    yellow                                          6    Br     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3                                              greenish                                                                               413                                                                    yellow                                          7    Br     C.sub.3 H.sub.6    greenish                                                                               413                                                                    yellow                                          8    CF.sub.3                                                                              C.sub.2 H.sub.4    greenish                                                                               417                                                                    yellow                                          9    CF.sub.3                                                                              C.sub.3 H.sub.6    greenish                                                                               408                                                                    yellow                                          10   CF.sub.3                                                                               ##STR91##         greenish yellow                                                                        408                                     11   CF.sub.3                                                                              (CH.sub.2).sub.6   greenish                                                                               408                                                                    yellow                                          12   CF.sub.3                                                                              (CH.sub.2).sub.3 O(CH.sub.2).sub.3                                                                greenish                                                                               408                                                                    yellow                                          13   Cl     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3                                              greenish                                                                               412                                                                    yellow                                          14   Cl     (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                                              greenish                                                                               413                                                                    yellow                                          15   Cl     CH.sub.2(CH.sub.3).sub.2CH.sub.2                                                                  greenish                                                                               413                                                                    yellow                                          ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                          ##STR92##                                                                     No.  A                R.sup.1                                                                               R.sup.2   Hue                                     ______________________________________                                          1   CH.sub.2 CH.sub.2                                                                               Cl     C.sub.2 H.sub.4 OH                                                                       golden                                                                         yellow                                   2   (CH.sub.2).sub.3 Cl     C.sub.2 H.sub.4 OH                                                                       golden                                                                         yellow                                   3   (CH.sub.2).sub.3 Cl     C.sub.3 H.sub.6 OH                                                                       golden                                                                         yellow                                   4   (CH.sub.2).sub.3 Cl     C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                      golden                                                                         yellow                                   5   (CH.sub.2).sub.3 Cl     C.sub.2 H.sub.4 OCH.sub.3                                                                golden                                                                         yellow                                   6   (CH.sub.2).sub.3 Cl     C.sub.3 H.sub.6 OCH.sub.3                                                                golden                                                                         yellow                                   7   (CH.sub.2).sub.4 Cl     C.sub.2 H.sub.4 OH                                                                       golden                                                                         yellow                                   8   (CH.sub.2).sub.4 Cl     C.sub.3 H.sub.6 OH                                                                       golden                                                                         yellow                                   9   (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3                                            Cl     C.sub.2 H.sub.4 OH                                                                       golden                                                                         yellow                                  10   (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3                                            Cl     C.sub.3 H.sub.6 OH                                                                       golden                                                                         yellow                                  11   (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                                            Cl     C.sub.3 H.sub.6 OH                                                                       golden                                                                         yellow                                  12   (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                                            Cl     C.sub.2 H.sub.4 OCH.sub.3                                                                golden                                                                         yellow                                  13   (CH.sub.2).sub. 3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                                           Cl     C.sub.3 H.sub.6 OCH.sub.3                                                                golden                                                                         yellow                                  14   (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                                            CF.sub.3                                                                              C.sub.3 H.sub.6 OCH.sub.3                                                                golden                                                                         yellow                                  15   (CH.sub.2).sub.3 CF.sub.3                                                                              C.sub.3 H.sub.6 OCH.sub.3                                                                golden                                                                         yellow                                  16   (CH.sub.2).sub.6 Cl     C.sub.2 H.sub.4 OCH.sub.3                                                                golden                                                                         yellow                                  17                                                                                   ##STR93##       Cl     C.sub.2 H.sub.4 OH                                                                       golden  yellow                          18                                                                                   ##STR94##       Cl     C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                      golden  yellow                          19   (CH.sub.2).sub.3 Cl     C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                      golden                                                                         yellow                                  20   (CH.sub.2).sub.3 Cl     C.sub.4 H.sub.8 OH                                                                       golden                                                                         yellow                                  21   (CH.sub.2).sub.3 CH.sub.3                                                                              C.sub.2 H.sub. 4 OH                                                                      golden                                                                         yellow                                  ______________________________________                                    

                                      TABLE 7                                      __________________________________________________________________________      ##STR95##                                                                                                          λmax                               No.                                                                               R    R.sup.1                                                                          R.sup.2                                                                             K                 Hue (nm)                                      __________________________________________________________________________      1 H CH.sub.3 Cl                                                                       H H Cl                                                                           SO.sub.2 C.sub.6 H.sub.5 SO.sub.2 C.sub.6 H.sub.5 Cl                                 ##STR96##        orange orange orange                           4 H CH.sub.3                                                                          Cl Cl                                                                            SO.sub.2 C.sub.6 H.sub.5 SO.sub.2 C.sub.6 H.sub.5                                    ##STR97##        orange orange                                  6 Cl Cl                                                                               Cl H                                                                             Cl SO.sub.2 C.sub.6 H.sub.5                                                          ##STR98##        orange orange                                  8 H H H                                                                               H H H                                                                            COCH.sub.3 CF.sub.3 COC.sub.6 H.sub.5                                                ##STR99##        orange orange orange                          11 12 13                                                                          H H F                                                                               H H H                                                                            COC.sub.6 H.sub.5 COCH.sub.3 Br                                                      ##STR100##       orange orange orange                          14 15                                                                             Br Cl                                                                               H H                                                                              F F                                                                                  ##STR101##       orange orange                                 16 17 18 19                                                                       H Cl SO.sub.2 C.sub.4 H.sub.9 Cl                                                    Cl H H Cl                                                                        Cl SO.sub.2 C.sub.4 H.sub.9 Cl Cl                                                    ##STR102##       orange orange orange orange                                                        425                                       20 21                                                                             Cl Cl                                                                               Cl H                                                                             Cl CH.sub.3                                                                          ##STR103##       orange orange                                                                      425                                       __________________________________________________________________________

                  TABLE 8                                                          ______________________________________                                          ##STR104##                                                                                                        λmax                                No.  R.sup.1           R.sup.2      (nm)                                       ______________________________________                                               ##STR105##       C.sub.6 H.sub.5                                                                             432                                        2                                                                                    ##STR106##                                                                                       ##STR107##  433                                        3                                                                                    ##STR108##                                                                                       ##STR109##  432                                        4                                                                                    ##STR110##                                                                                       ##STR111##  435                                        5                                                                                    ##STR112##                                                                                       ##STR113##  435                                        6                                                                                    ##STR114##                                                                                       ##STR115##  434                                        7                                                                                    ##STR116##       C.sub.6 H.sub.5                                                                             430                                        8                                                                                    ##STR117##                                                                                       ##STR118##  432                                        9                                                                                    ##STR119##                                                                                       ##STR120##  430                                        10                                                                                   ##STR121##                                                                                       ##STR122##  430                                        11                                                                                   ##STR123##       C.sub.6 H.sub.5                                                                             430                                        12                                                                                   ##STR124##                                                                                       ##STR125##  435                                        13                                                                                   ##STR126##                                                                                       ##STR127##  431                                        ______________________________________                                    

EXAMPLE 5

19.5 parts of 2,4-dichloroaniline-5-sulfonic acid are stirred overnight with 50 parts of 15% strength hydrochloric acid in the presence of a wetting agent which is effective under acidic conditions. Thereafter, the mixture is cooled with ice to 0° C., 27 parts by volume of a 23% strength sodium nitrite solution are added in the course of from 5 to 20 minutes, and the suspension is stirred for a further 3 hours at from 0° to 5° C. A solution or suspension of 21.2 parts of 2,6-bis-(3-hydroxypropylamino)-3-cyano-4-methylpyridine in 120 parts by volume of water and 7 parts by volume of concentrated hydrochloric acid is then run in. Stirring is continued for from 15 to 30 minutes, and the pH of the mixture is then slowly increased to 1-1.5 by adding sodium hydroxide solution or sodium formate. The acid formed as a result of the coupling reaction is then bound continuously by adding appropriate amounts of sodium hydroxide solution or sodium formate. When the mixture has been kept at pH 1-1.5 for about 30-60 minutes, the pH is increased to 3-3.5 by adding dilute sodium hydroxide solution or sodium acetate. The coupling reaction quickly comes to an end. The resulting dye of the formula ##STR128## is precipitated virtually quantitatively by adding 40 parts of sodium chloride and is then isolated by filtration. After drying, 44 parts of a brown powder are obtained.

The dye dissolves in water to give a yellow solution and dyes nylon and wool in intense, lightfast, golden yellow hues.

The absorption maximum of a solution of about 0.020 part of the dye in 900 parts by volume of dimethylformamide and 150 parts by volume of glacial acetic acid is 457 nm (water: 435 nm).

                  TABLE 9                                                          ______________________________________                                          ##STR129##                                                                    No.  R.sup.1          R.sup.2      λmax (nm)                            ______________________________________                                               ##STR130##      C.sub.6 H.sub.5                                                                             459                                         2                                                                                    ##STR131##                                                                                      ##STR132##  459                                         3                                                                                    ##STR133##                                                                                      ##STR134##  459                                         4                                                                                    ##STR135##                                                                                      ##STR136##  460                                         5                                                                                    ##STR137##                                                                                      ##STR138##  460                                         6                                                                                    ##STR139##                                                                                      ##STR140##  460                                         7                                                                                    ##STR141##      C.sub.6 H.sub.5                                                                             456                                         8                                                                                    ##STR142##                                                                                      ##STR143##  459                                         9                                                                                    ##STR144##                                                                                      ##STR145##  457                                         10                                                                                   ##STR146##                                                                                      ##STR147##  457                                         11                                                                                   ##STR148##      C.sub.6 H.sub.5                                                                             458                                         12                                                                                   ##STR149##                                                                                      ##STR150##  460                                         13                                                                                   ##STR151##                                                                                      ##STR152##  458                                         ______________________________________                                    

                                      TABLE 10                                     __________________________________________________________________________      ##STR153##                                                                    No.                                                                               R  R.sup.1    R.sup.2    R.sup.3                                                                           Hue     λmax (nm)                        __________________________________________________________________________      1 Cl H          C.sub.3 H.sub.6 OCH.sub.3                                                                 C.sub.3 H.sub.7                                                                   yellow  446                                      2 Cl H          C.sub.3 H.sub.6 OH                                                                        C.sub.3 H.sub.7                                                                   yellow  446                                      3 Cl H          C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                       CH.sub.3                                                                          yellow  441                                      4 Cl H          C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                       H  yellow  443                                      5 Cl H          C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                       CH.sub.3                                                                          yellow  443                                      6 Cl H          C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                                CH.sub.3                                                                          yellow  444                                      7 Cl H          C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                      CH.sub.3                                                                          yellow  446                                       8                                                                               Cl H          C.sub.3 H.sub.6 OCH.sub.3                                                                 CH.sub.3                                                                          yellow  446                                      9 Cl H          C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                          CH.sub.3                                                                          yellow  446                                     10 Cl C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                       H          CH.sub.3                                                                          yellow  448                                     11 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                         H          CH.sub.3                                                                          yellow  449                                     12 Cl C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.4 OH                                                                        CH.sub.3                                                                          golden yellow                                                                          455                                     13 Cl CH.sub.3   C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                       CH.sub.3                                                                          golden yellow                                                                          454                                     14 Cl C.sub.2 H.sub.5                                                                           C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                       CH.sub.3                                                                          golden yellow                                                                          455                                     15 Cl C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                       CH.sub.3                                                                          golden yellow                                                                          453                                     16 Cl CH.sub.2 CHCH.sub.2                                                                       C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                       CH.sub.3                                                                          golden yellow                                                                          454                                     17 Cl CH(CH.sub.3).sub.2                                                                        C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                       CH.sub.3                                                                          golden yellow                                                                          453                                     18 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.3                                                                          golden yellow                                                                          454                                     19 Cl (CH.sub.2).sub.3 OCH.sub.3                                                                CH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.3                                                                          golden yellow                                                                          455                                     20 Cl (CH.sub.2).sub.3 OCH.sub.3                                                                (CH.sub.2).sub.3 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          456                                     21 Cl                                                                                 ##STR154##                                                                               C.sub.2 H.sub.4 OCH.sub.3                                                                 CH.sub.3                                                                          golden yellow                                                                          455                                     22 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                               (CH.sub.2).sub.3 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          455                                     23 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 CH.sub.2 OH                                                                      CH.sub.3                                                                          golden yellow                                                                          453                                     24 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                                ##STR155##                                                                               CH.sub.3                                                                          golden yellow                                                                          453                                     25 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                        CH.sub.3                                                                          golden yellow                                                                          452                                     26 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                               (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                                                      CH.sub.3                                                                          golden yellow                                                                          454                                     27 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                               (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH                                                     CH.sub.3                                                                          golden yellow                                                                          454                                     28 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                                               (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          454                                     29 Cl                                                                                 ##STR156##                                                                               CH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.3                                                                          golden yellow                                                                          452                                     30 Cl                                                                                 ##STR157##                                                                               (CH.sub.2).sub.3 OCH.sub.3                                                                CH.sub.3                                                                          orange  453                                     31 Cl                                                                                 ##STR158##                                                                               (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          452                                     32 Cl                                                                                 ##STR159##                                                                               (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          orange  453                                     33 Cl                                                                                 ##STR160##                                                                               (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                         CH.sub.3                                                                          orange  453                                     34 Cl                                                                                 ##STR161##                                                                                ##STR162##                                                                               CH.sub.3                                                                          orange  453                                     35 Cl (CH.sub.2).sub.3 OH                                                                       (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          452                                     36 Cl (CH.sub.2).sub.3 OH                                                                        ##STR163##                                                                               CH.sub.3                                                                          golden yellow                                                                          455                                     37 Cl (CH.sub.2).sub.3 OH                                                                       (CH.sub.2).sub.2 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          453                                     38 Cl (CH.sub. 2).sub.3 OH                                                                      (CH.sub.2).sub.3 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          456                                     39 Cl (CH.sub.2).sub.3 OH                                                                       (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                         CH.sub.3                                                                          golden yellow                                                                          456                                     40 Cl (CH.sub.2).sub.2 OH                                                                       (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          452                                     41 Cl (CH.sub.2).sub.2 OH                                                                       (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          453                                     42 Cl (CH.sub.2).sub.2 OH                                                                        ##STR164##                                                                               CH.sub.3                                                                          golden yellow                                                                          453                                     43 Cl (CH.sub.2).sub.2 OH                                                                       (CH.sub.2).sub.2 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          451                                     44 Cl (CH.sub.2).sub.2 OH                                                                       (CH.sub.2).sub.2 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          453                                     45 Cl (CH.sub.2).sub.2 OH                                                                       (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                         CH.sub.3                                                                          golden yellow                                                                          453                                     46 Cl (CH.sub.2).sub.2 OH                                                                       C.sub.4 H.sub.9 (n)                                                                       CH.sub.3                                                                          golden yellow                                                                          456                                     47 Cl (CH.sub.2).sub.2 OH                                                                       (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                CH.sub.3                                                                          golden yellow                                                                          455                                     48 Cl (CH.sub.2).sub.2 OH                                                                       (CH.sub.2).sub.2 C.sub.6 H.sub. 5                                                         Ch.sub.3                                                                          golden yellow                                                                          450                                     49 Cl (CH.sub.2).sub.2 OH                                                                        ##STR165##                                                                               CH.sub.3                                                                          golden yellow                                                                          455                                     50 Cl (CH.sub.2).sub.2 OH                                                                        ##STR166##                                                                               CH.sub.3                                                                          golden yellow                                                                          454                                     51 Cl C.sub.2 H.sub.5                                                                            ##STR167##                                                                               CH.sub.3                                                                          golden yellow                                                                          451                                     52 Cl C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                           CH.sub.3                                                                          golden yellow                                                                          449                                     53 Cl (CH.sub.2).sub.2 CN                                                                       (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          450                                     54 Cl (CH.sub.2).sub.5 CN                                                                       (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          457                                     55 Cl (CH.sub.2).sub.2 C.sub.6 H.sub.5                                                          (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          448                                     56 Cl                                                                                 ##STR168##                                                                               C.sub.4 H.sub.9 (n)                                                                       CH.sub.3                                                                          golden yellow                                                                          450                                     57 Cl CH.sub.2 CHCH.sub. 2                                                                      (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          452                                     58 Cl CH.sub.2 CHCH.sub.2                                                                       (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          454                                     59 Br (CH.sub.2).sub.3 OH                                                                       (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          457                                     60 CF.sub.3                                                                          (CH.sub.2).sub.3 OH                                                                       (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          458                                     61 CF.sub.3                                                                          (CH.sub.2).sub.2 OCH.sub.3                                                                (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          456                                     62 Cl                                                                                 ##STR169##                                                                               (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          453                                     63 Cl                                                                                 ##STR170##                                                                               (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          454                                     64 Cl                                                                                 ##STR171##                                                                               (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          455                                     65 Cl                                                                                 ##STR172##                                                                               (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          454                                     66 Cl (CH.sub.2).sub.2 OCOCH.sub.3                                                              (CH.sub.2).sub.2 OCOCH.sub.3                                                              CH.sub.3                                                                          golden yellow                                                                          450                                     67 Cl (CH.sub.2).sub.3 OCHO                                                                     (CH.sub.2).sub.3 OCHO                                                                     CH.sub.3                                                                          golden yellow                                                                          454                                     68 Cl (CH.sub.2).sub.2 OCH.sub.3                                                                (CH.sub.2).sub.3 OCHO                                                                     CH.sub.3                                                                          golden yellow                                                                          453                                     69 Cl (CH.sub.2).sub.3 OCHO                                                                     (CH.sub.2).sub.2 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          453                                     70 Cl (CH.sub.2).sub.4 OH                                                                       (CH.sub.2).sub.4 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          457                                     71 Cl (CH.sub.2).sub.4 OH                                                                       (CH.sub.2).sub.3 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          457                                     72 Cl (CH.sub.2).sub.4 OH                                                                       (CH.sub.2).sub.2 OH                                                                       CH.sub.3                                                                          golden yellow                                                                          456                                     73 Cl (CH.sub.2).sub.4 OH                                                                       (CH.sub.2).sub.2 OCH.sub.3                                                                CH.sub.3                                                                          golden yellow                                                                          456                                     74 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                                                 ##STR173##                                                                               CH.sub.3                                                                          orange  459                                     75 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                                                C.sub.6 H.sub.5                                                                           CH.sub.3                                                                          orange  458                                     76 Cl C.sub.3 H.sub.5 (OC.sub.2 H.sub.4).sub.2 OCH.sub.3                                        C.sub.6 H.sub.5                                                                           CH.sub.3                                                                          orange  458                                     77 Cl C.sub.3 H.sub.6 (OC.sub.2 H.sub.4).sub.2 OCH.sub.3                                         ##STR174##                                                                               CH.sub.3                                                                          orange  460                                     78 Cl C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                        ##STR175##                                                                               CH.sub.3                                                                          orange  458                                     79 Cl C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                       C.sub.6 H.sub.5                                                                           CH.sub.3                                                                          orange  457                                     80 Cl C.sub.6 H.sub.5                                                                           C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                       CH.sub.3                                                                          orange  456                                     81 Cl                                                                                 ##STR176##                                                                               C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                       CH.sub.3                                                                          orange  458                                     82 Cl                                                                                 ##STR177##                                                                               C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                       CH.sub.3                                                                          orange  458                                     83 Cl                                                                                 ##STR178##                                                                               C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                       CH.sub.3                                                                          orange  458                                     __________________________________________________________________________

                                      TABLE 11                                     __________________________________________________________________________      ##STR179##                                                                                                                   λmax                     No.                                                                               R  R.sup.1      R.sup.2   R.sup.3   Hue     (nm)                            __________________________________________________________________________      1 Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OH                                                                       golden yellow                                                                          435                              2 Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                golden yellow                                                                          433                              3 Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OCH.sub.3                                                                golden yellow                                                                          436                              4 Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                         golden yellow                                                                          434                              5 Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                      yellow  433                               6                                                                               Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                               yellow  433                              7 Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH                                                      golden yellow                                                                          435                              8 Cl C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                      golden yellow                                                                          436                              9 Cl C.sub.2 H.sub.4 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                yellow  431                             10 Cl C.sub.2 H.sub.4 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OCH.sub.3                                                                yellow  432                             11 Cl C.sub.2 H.sub.4 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OC.sub.3 H.sub.7                                                         yellow  433                             12 Cl C.sub.2 H.sub.4 OCH.sub.3                                                                   C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                yellow  431                             13 Cl C.sub.2 H.sub.4 OCH.sub.3                                                                   C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OCH.sub.3                                                                yellow  433                             14 Cl C.sub.3 H.sub.6 OCH.sub.3                                                                   C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OCH.sub.3                                                                golden yellow                                                                          434                             15 Cl                                                                                 ##STR180##  C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.4 OCH.sub.3                                                                golden yellow                                                                          435                             16 Cl                                                                                 ##STR181##  C.sub.6 H.sub.5                                                                           ##STR182##                                                                              golden yellow                                                                          436                             17 Br                                                                                 ##STR183##  C.sub.6 H.sub.5                                                                           ##STR184##                                                                              golden yellow                                                                          436                             18 Br C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.6                                                                          C.sub.3 H.sub.6 OH                                                                       golden yellow                                                                          437                             19 Cl C.sub.3 H.sub.6 OH                                                                           ##STR185##                                                                              C.sub.3 H.sub.6 OH                                                                       golden yellow                                                                          436                             20 Cl C.sub.3 H.sub.6 OH                                                                           ##STR186##                                                                              C.sub.3 H.sub.6 OH                                                                       golden yellow                                                                          437                             21 Cl C.sub.4 H.sub.8 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.4 H.sub.8 OH                                                                       golden yellow                                                                          438                             22 Cl C.sub.2 H.sub.4 OH                                                                           ##STR187##                                                                              C.sub.2 H.sub.4 OH                                                                       golden yellow                                                                          436                             23 Cl                                                                                 ##STR188##                                                                                  ##STR189##                                                                              C.sub.2 H.sub.4 OH                                                                       yellow  434                             24 CF.sub.3                                                                          C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.3 H.sub.6 OH                                                                       golden yellow                                                                          439                             25 CF.sub.3                                                                          C.sub.3 H.sub.6 OH                                                                          C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OH                                                                       golden yellow                                                                          439                             26 CF.sub.3                                                                           ##STR190##  C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.4 OH                                                                       golden yellow                                                                          439                             __________________________________________________________________________

                                      TABLE 12                                     __________________________________________________________________________      ##STR191##                                                                    No.                                                                               A            R.sup.1                                                                           R.sup.2 Hue     λmax (nm)                            __________________________________________________________________________     1  CH.sub.2 CH.sub.2                                                                           Cl C.sub.2 H.sub.4 OH                                                                     golden yellow                                                                          451                                         2  (CH.sub.2).sub.3                                                                            Cl C.sub.2 H.sub.4 OH                                                                     golden yellow                                                                          453                                         3  (CH.sub.2).sub.3                                                                            Br C.sub.3 H.sub.6 OH                                                                     golden yellow                                                                          455                                         4  (CH.sub.2).sub.3                                                                            Cl C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                    golden yellow                                                                          455                                         5  (CH.sub.2).sub.3                                                                            Cl C.sub.2 H.sub.4 OCH.sub.3                                                              golden yellow                                                                          455                                         6  (CH.sub.2).sub.3                                                                            Cl C.sub.3 H.sub.6 OCH.sub.3                                                              golden yellow                                                                          456                                         7  (CH.sub.2).sub.4                                                                            Cl C.sub.2 H.sub.4 OH                                                                     golden yellow                                                                          453                                         8  (CH.sub.2).sub.4                                                                            Cl C.sub.3 H.sub.6 OH                                                                     golden yellow                                                                          456                                         9  (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3                                        Cl C.sub.2 H.sub.4 OH                                                                     golden yellow                                                                          452                                         10 (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3                                        Cl C.sub.3 H.sub.6 OH                                                                     golden yellow                                                                          453                                         11 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                                        Cl C.sub.3 H.sub.6 OH                                                                     golden yellow                                                                          453                                         12 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                                        Cl C.sub.2 H.sub.4 OCH.sub.3                                                              golden yellow                                                                          452                                         13 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                                        Br C.sub.3 H.sub.6 OCH.sub.3                                                              golden yellow                                                                          454                                         __________________________________________________________________________

                                      TABLE 13                                     __________________________________________________________________________      ##STR192##                                                                                                         λmax                               No.                                                                               R.sup.1                                                                              R.sup.2                                                                          R.sup.3                                                                          R.sup.4      R.sup.5                                                                               Hue (nm)                                      __________________________________________________________________________      1 N(CH.sub.3).sub.2                                                                    H H CH.sub.2 CH.sub.2 OH                                                                        CH.sub.2 CH.sub.2 OH                                                                  orange                                         2 N(CH.sub.3).sub.2                                                                    H Cl                                                                               CH.sub.2 CH.sub.2 OH                                                                        CH.sub.2 CH.sub.2 OH                                                                  orange                                                                             430                                        3 N(CH.sub.3).sub.2                                                                    Cl                                                                               Cl                                                                               CH.sub.2 CH.sub.2 OH                                                                        CH.sub.2 CH.sub.2 OH                                                                  orange                                                                             463                                        4 N(C.sub.2 H.sub.5).sub.2                                                             Cl                                                                               Cl                                                                               CH.sub.2 CH.sub.2 OH                                                                        CH.sub.2 CH.sub.2 OH                                                                  orange                                                                             463                                        5 N(C.sub.2 H.sub.5).sub.2                                                             H Cl                                                                               CH.sub.2 CH.sub.2 OH                                                                        CH.sub.2 CH.sub.2 OH                                                                  orange                                                                             461                                        6 N(C.sub.2 H.sub.5).sub.2                                                             H Cl                                                                               C.sub.3 H.sub.6 OH                                                                          C.sub.3 H.sub.6 OH                                                                    orange                                                                             432                                        7 N(CH.sub.3).sub.2                                                                    Cl                                                                               Cl                                                                               C.sub.2 H.sub.4 OCH.sub.3                                                                   C.sub.3 H.sub.6 OH                                                                    orange                                                                             463                                        8 N(CH.sub.3).sub.2                                                                    Cl                                                                               Cl                                                                               C.sub.2 H.sub.4 OCH.sub.3                                                                   C.sub.2 H.sub.4 OCH.sub.3                                                             orange                                                                             462                                        9 N(CH.sub.3).sub.2                                                                    Cl                                                                               Cl                                                                               C.sub.3 H.sub.6 OCH.sub.3                                                                   C.sub.3 H.sub.6 OCH.sub.3                                                             orange                                                                             465                                       10 N(CH.sub.3).sub.2                                                                    Cl                                                                               Cl                                                                                ##STR193##  C.sub.3 H.sub.6 OCH.sub.3                                                             orange                                                                             462                                       11 N(CH.sub.3).sub.2                                                                    Cl                                                                               Cl                                                                                ##STR194##  C.sub.2 H.sub.4 OH                                                                    orange                                                                             461                                       12 N(CH.sub.3).sub.2                                                                    Cl                                                                               Cl                                                                                ##STR195##  C.sub.2 H.sub.5                                                                       orange                                                                             466                                       13 N(CH.sub.3).sub.2                                                                    Cl                                                                               Cl                                                                                ##STR196##                                                                                  ##STR197##                                                                           orange                                                                             467                                       14 N(C.sub.2 H.sub.5).sub.2                                                             Cl                                                                               Cl                                                                                ##STR198##                                                                                  ##STR199##                                                                           orange                                                                             467                                       15 N(C.sub.2 H.sub.5).sub.2                                                             H H                                                                                 ##STR200##                                                                                  ##STR201##                                                                           orange                                                                             453                                       16 N(C.sub.2 H.sub.5).sub.2                                                             H H                                                                                 ##STR202##  C.sub.6 H.sub.5                                                                       orange                                                                             452                                       17 N(C.sub.2 H.sub.5).sub.2                                                             H H C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                         C.sub.6 H.sub.5                                                                       orange                                                                             452                                       18 N(CH.sub.3).sub.2                                                                    H H C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                         C.sub.6 H.sub.5                                                                       orange                                                                             452                                       19 CH.sub.3                                                                             H Cl                                                                                ##STR203##  C.sub.6 H.sub.5                                                                       orange                                                                             444                                       20 CH.sub.3                                                                             H Cl                                                                                ##STR204##                                                                                  ##STR205##                                                                           orange                                                                             445                                       21 N(CH.sub.3).sub.2                                                                    Cl                                                                               Cl                                                                               C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                                                  C.sub.3 H.sub.6 OCH.sub.3                                                             orange                                                                             465                                       22 NHC.sub.4 H.sub.9                                                                    Cl                                                                               Cl                                                                                ##STR206##  C.sub.6 H.sub.5                                                                       orange                                                                             463                                       __________________________________________________________________________

                  TABLE 14                                                         ______________________________________                                          ##STR207##                                                                                                         λmax                               No.     R.sup.1 R.sup.2        Hue   (nm)                                      ______________________________________                                         1       Cl      C.sub.2 H.sub.4 OC.sub.4 H.sub.9                                                              yellow                                                                               426                                       2       Cl      C.sub.3 H.sub.6 OC.sub.4 H.sub.9                                                              yellow                                                                               427                                       3       Cl      C.sub.4 H.sub.9 (n)                                                                           yellow                                                                               428                                       4       Cl      C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                              yellow                                                                               426                                       5       Cl      C.sub.3 H.sub.6 OCH.sub.3                                                                     yellow                                                                               427                                       6       Cl      C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                                                    yellow                                                                               427                                       7       CH.sub.3                                                                               C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                                                    yellow                                                                               427                                       8       CH.sub.3                                                                               C.sub.3 H.sub.6 OCH.sub.3                                                                     yellow                                                                               427                                       9       CH.sub.3                                                                               C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                              yellow                                                                               427                                       10      CH.sub.3                                                                               C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH                                                           yellow                                                                               427                                       11      Cl      C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                           yellow                                                                               427                                       12      CH.sub.3                                                                               C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                           yellow                                                                               427                                       ______________________________________                                    

                  TABLE 15                                                         ______________________________________                                          ##STR208##                                                                                                           λmax                             No. R.sup.1    R.sup.2  R.sup.3  Hue   (nm)                                    ______________________________________                                          1 C.sub.2 H.sub.4 OCH.sub.3                                                                  CH.sub.3 CH.sub.3 yellow                                                                               418                                      2 C.sub.2 H.sub.4 OCH.sub.3                                                                  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                         yellow                                                                               419                                      3 C.sub.3 H.sub.6 OCH.sub.3                                                                  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                         yellow                                                                               420                                      4 C.sub.3 H.sub.6 OCH.sub.3                                                                  CH.sub.3 CH.sub.3 yellow                                                                               418                                      5 C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                           CH.sub.3 CH.sub.3 yellow                                                                               418                                      6 C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                           C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                         yellow                                                                               420                                      ##STR209##    C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                         yellow                                                                               419                                      ##STR210##    C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                         yellow                                                                               420                                      ##STR211##    C.sub.4 H.sub.9 (n)                                                                     C.sub.4 H.sub.9 (n)                                                                     yellow                                                                               422                                     ______________________________________                                     

I claim:
 1. A compound of the formula ##STR212## wherein X¹ is chlorine, bromine, methyl or trifluoromethyl, Y³ is chlorine or bromine, and K¹ is a radical of the formula ##STR213## where R³ is C₂ to C₄ hydroxyalkyl, methoxyalkyl or methoxypropyl.
 2. The compound of claim 1, which is: ##STR214## 